91PORNY

Oh, the awkwardness! Believe me, I know it well. I'm the one who walks around for hours with my skirt tucked into my undies, drags toilet paper on my heel all day, or blurts out the absolute wrong thing at the wrong moment. With an entire lifetime of living through agonizingly awkward situations, I know it when I see it (or speak it). And this round-up of awkward conversations lives rent-free in my head. If you, like me, frequently (and unintentionally) make it awkward, these cringeworthy convos could help you feel less alone. 

I'll start by telling on myself.  I am the queen of saying awkward things. They sound fine in my mind, but as soon as they're out of my mouth? They live rent-free in my head for weeks — or sometimes years. Fortunately, my friends are used to it.

My girlfriends and I get a condo together at the beach every year. One year, I was sharing a room with my friend, Kristen. I walked into our room, and she was in her underwear, bent over, picking something up off the floor. It felt awkward, so to ease the awkwardness, I said to her, "Don't worry. I've seen worse." Which, of course, made it more awkward. It wasn't the reassuring comment it sounded like in my head.

Next, I'm going to tell on one of my friends. While I'm pretty active now, I haven't always been in the greatest of shape, but I made a real committment in the past year to return to my active youth roots (funny how middle age will do that to you). So I was out hiking with a friend recently, and we got to a rough part of the terrain. I've been hiking a lot, and I've hiked this spot many times, but I know it can look a little daunting when you first try it, so I told her we could take it slow. Her response? "Don't worry. If you can do it, anyone can." My husband and I often joke now whenever I do something hard that, "If Karen can do it..."

Related: How to Be Less Awkward: 10 Tips That Really Work

One of my co-workers, Kate, tells this story:

In college, I was super into my long-distance boyfriend, who lived in the dorms at a different school. He and his roommate plastered their door with funny comics and write-ups. One weekend, I drove four hours to see him, and he met me outside his room.

“You have to read this,” he said, pointing to a long write-up posted on the door. I had to pee really badly after driving for so long, so I only pretended to read it, saying, “Ha! That’s so hilarious!” He stared at me in shock and profoundly disappointed judgment: “What is wrong with you? You think that’s funny?! They’re marking women with cattle brands!”

Lesson learned: Just tell people you have to pee and will read things later.

Another co-worker, Megan, shares one of her most awkward conversations.

During Covid, when I was working at the grocery store, the assistant store manager grew a MASSIVE beard, but because of the masks, I didn’t realize it. Cut to right after the mask mandate had been lifted. I caught him coming out of the back room and did a full double-take and then said “Well, THAT’s a look,” not realizing just how rude it sounded.

Thank goodness this one only happened in front of my hubby, who is used to me saying weird stuff. But he still reminds me of this, 20 years later.

To be fair, I was tired. But I still said it. We were listening to music in the car, and Queen's song Under Pressure was playing on the car stereo. 

"Wow! Freddy really sounds like David Bowie in this song," I said without thinking. That's because it was (which I absolutely knew) a Queen & Bowie collab. 

A few years ago, my husband and I took a road trip where we visited the sacred indigenous site Devil's Tower in Wyoming (prominently featured in Close Encounters of the Third Kind). It was so beautiful and felt sacred while we were there.

We stopped at Mount Rushmore on our way through South Dakota the next day. As we were coming down the escalator into the parking lot, I overheard a woman who had clearly had a similar itinerary to ours say this: "This was so much better than that Indian site we visited yesterday. You know what would've made that better? If they'd carved a face in it." Now, whenever we're faced with some wonder of nature, we always joke that it would look better if they'd carve a face in it. 

Sorry mom....

One Thanksgiving, my mom pointed me towards the wine rack in their kitchen that had a few bottles of red wine in it. She said, "You can open one of these bottles of wine if you want, but I'm not sure how fresh it is." Apparently, she'd never heard of aging red wine. 

When I was in my early 20s, I worked as a personal trainer at a gym. I formed what I thought was a friendship with a guy who was probably in his 50s. We never hung out, but I'd chat with him at the gym and thought he was a nice, paternal older guy. Then, one day, he told me he was into me. I was shocked because I thought maybe he looked at me like a daughter or something.  Before I even knew what I was saying, I blurted out, "But you're old!" (He was probably younger than I am right now.)

Another one from Kate:

My kids have this great pediatrician, who in addition to being a really good doctor, says the sweetest things like, “How can you be turning 12 when your mom still looks so young?” He’s older than I am, but it’s hard to know how much older because men are tricky that way. Because I struggle with anxiety, I was worrying about what would happen if he retired before the kids grew up, so I blurted out, “You’re not retiring soon, are you?” He looked at me in this wounded way and said, “Do I look old enough to retire? I’m not that old!”

I grew up attending church, but I didn't really go much as an adult. When my son was in middle school, he joined a handbells choir at a local church because his friend was in it, so every once in a while, I'd have to go to a church service to watch him perform. During the service, they'd have everyone stand up, shake hands with their neighbors, and say something nice. As a somewhat socially anxious person, I worried about this happening at every service. Where would I turn? Who would I shake hands with? What if nobody talked to me? It was the stuff of nightmares. So, at one such service, a nice lady next to me turned, shook my hand, and said, "God bless." My response... "Who?"

Cute guy at the gym asked me my name. My brain froze up for a minute, and I blurted, "Kathy." My name's not Kathy, but that's what he called me. 

I told someone to have a nice day. What's so awkward about that? It was as I was leaving their father's funeral. Thing is, I was already flustered because right before that exchange, he'd said to me, "Thanks for coming," and my response was, "You, too." This was years ago, and I still have hot flashes when I think about it.

When my five-year-old step daughter first introduced her father to her teacher, she said this: "This is my dad. His farts are atrocious."

Another one from Megan:

When my 9-year-old niece was 5, she said, "I'm half-white, half-PANIC."

According to Megan, her dad is Puerto Rican, so they think she was trying to say "Hispanic." I prefer to think she knew what it was like to live in my mind. 

It's not easy to be awkward... emotionally, anyway. But it seems that I'm exceptionally good at it, and so are so many other people. Sometimes, the words just tumble out before we think, and the result is incredibly cringeworthy. So the next time you lie awake staring at the ceiling thinking about all the things you could've said instead of that totally awkward thing, remember you're not alone. I'll be lying in my bed under the same sky, staring at my ceiling, too.